An unprecedented 7-membered ring enamide cyclization through hypervalent iodine phenolic oxidation. Issue 23 (6th June 2018)

• Record Type: Journal Article
• Authors: Berthiol, Florian; Philouze, Christian; Chavant, Pierre Y.; Poisson, Jean-François
• Is Part Of: Tetrahedron letters. Volume 59:Issue 23(2018)
• Page Start: 2293
• Page End: 2295
• Publication Date: 2018-06-06
• Subjects: 7-Membered ring cyclization -- Enamide -- Hypervalent iodine -- Phenolic oxidation -- Galanthamine; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.05.013
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: An original hypervalent iodine promoted 7-membered ring cyclization was discovered. An unusual and surprisingly stable hemi-aminal was isolated. A new approach in the total synthesis of galanthamine was investigated. Abstract: An unprecedented 7-membered ring cyclization of an enamide to a phenol through hypervalent iodine phenolic oxidation was discovered. In the process a molecule of solvent is incorporated on the cycle forming an unusual and stable hemi-aminal ether.